I don’t like the stigma around salespeople.
Not just because I’m in sales. It bothered me before I got into sales.
Growing up, I pictured salespeople as scammy, pushy, arrogant, and annoying. But I also knew they made good money. I remember asking my grandma what our neighbor did for work, because the guy had a huge house. She just said, “Oh, he’s mean; he’s in sales.”
To me, that meant salespeople are loaded and salespeople are mean. I had two ideas stuck together that didn’t quite fit. Salespeople are kind of shady. Salespeople also do well for themselves. I didn’t reconcile that until I found myself in sales and wondered if being in sales made me a bad person.
Here’s what I’ve landed on: the salespeople who make the stigma true are either annoying people, or they’re being incentivized by their company in a way that makes them behave that way.
That second part matters more than it sounds like it should.
Why the Sales Stigma Exists
The stereotype didn’t come from nowhere. Enough people have sat across from a pushy salesperson, felt cornered into a decision, and walked away with something they didn’t really want. That experience sticks. It’s a lot more memorable than the quiet, boring transaction where someone just helped you get what you needed.
So the stigma survives because the loud, aggressive version of selling is the version people remember. The good version doesn’t announce itself. It just looks like someone helping you.
That’s the real problem with the stereotype. It’s not wrong about the salespeople it’s describing. It’s wrong about assuming that’s what selling has to look like.
Sometimes the Problem Is the Incentive
It’s easy to blame the person. Sometimes that’s fair. But a lot of pushy sales behavior isn’t really a character flaw, it’s a rational response to a bad system of the company they work for.
If a company tells a salesperson they need 100 calls a day, they need to close a deal by the end of the day, and they don’t get paid unless someone buys, you’ve built an environment where pushing people is the only move. Nobody trained that person to be honest about fit, because honesty about fit doesn’t show up on this week’s numbers.
Good salesperson plus bad incentives equals bad behavior. Good salesperson plus good incentives equals someone you’d actually recommend to a friend.
Same person. Different math.
To be fair, customers aren’t always innocent either. Some lie about their budget. Some collect quotes from five vendors just to squeeze the one they already picked. Some want free consulting with zero intention of buying anything. Sales isn’t a morality play with a clean villain. It’s two people trying to make a decision with incomplete information, and good sales is what happens when someone’s actually trying to close that gap instead of exploit it.
What Actually Makes a Good Salesperson
Being pushy, aggressive, or annoying doesn’t make you better at sales. Today it probably hurts you more than you’d think. It might close a deal here or there, but it isn’t building a relationship. Nobody refers a pushy salesperson to their friends. Nobody comes back to one the next time they have a problem.
A pushy, aggressive salesperson can more easily be replaced by AI because there’s no human connection involved.
The best salespeople I know aren’t salesy at all. They’re just genuinely helpful. They ask good questions, they actually listen to the answers, and they only recommend something once they fully understand what the person is dealing with.
That sounds obvious written out like that. It’s rare in practice because it requires giving up something that feels risky in the moment: the sale itself.
Persuasion vs. Manipulation
None of this means salespeople shouldn’t persuade anyone. Persuasion isn’t the problem.
Persuasion sounds like: “I think this is the right option for your situation, and here’s why.”
Manipulation sounds like: “This is the only option, and you have to make a decision now, or else.”
The first one respects the person’s ability to make their own decision. The second one is trying to route around it. That’s the line, not “salespeople should never try to convince anyone of anything.”
The Doctor Test
I like comparing it to a doctor. A doctor’s job is to figure out what’s actually wrong with you before telling you what to do about it. They ask questions, run tests, diagnose, and then give you options based on what they find.
I used to think the reason you trust a good doctor is that they don’t have a stake in the outcome. That’s not quite right. Doctors have incentives too, and there are bad doctors. Insurance relationships, hospital systems, whatever pharma rep took them to lunch last week. Nobody’s fully neutral.
The real reason you trust a good doctor is that you believe their recommendation is coming from your diagnosis, not from their incentive. You’re not expecting them to have zero self-interest. You’re just betting that they’re trying to make money by actually helping you, not by working around you.
Same bar applies to a salesperson. You don’t need to pretend they don’t want the sale. You just need to believe they want it because it’s genuinely right for you, not instead of that.
Knowing When Not to Sell
This might be the most useful skill I’ve learned in the job, and it’s the one most sales training skips: knowing when not to sell.
Sometimes the product isn’t a good fit. Sometimes the customer can’t really afford it. Sometimes a competitor is genuinely the better call. Sometimes the person doesn’t actually have the problem you solve. Sometimes they’re not ready, and pushing them just wastes everyone’s time.
A mediocre salesperson asks, “How do I get this person to buy?”
A good one asks, “Should this person buy at all?”
That second question is a completely different job. It’s the difference between someone trying to close you and someone trying to figure out if closing you is even the right thing to do.
Selling to People Who Don’t Want to Talk to a Salesperson
I work with engineers now, and most of them don’t want to talk to a salesperson at all. Honestly, I get it. I respect it.
But that doesn’t mean I can’t help. If someone doesn’t want to talk to me, I’ll get them in touch with the person on our team who actually speaks their language.
Engineers don’t hate salespeople. They hate being sold to. Those are different problems. My job isn’t to be the technical expert or to insert myself into every conversation. It’s to recognize when someone needs an answer I can’t give them, and get them to the person who can.
That’s not stepping back from the sale. It’s sales as orchestration instead of persuasion. Getting the right information to the right person is still doing the job, even if I’m not the one delivering it.
The Car Dealership Example
Say you walk into a dealership knowing exactly what you want, and they don’t have it. A good salesperson tells you, “I know a shop down the road that has that exact car.” Maybe they mention a couple alternatives first, but they’re straight with you about what they don’t have.
It’s honest.
They just sent you to a competitor.
They didn’t get the sale.
But that’s the moment that actually builds trust, because now you know they weren’t just trying to move a unit off the lot. They were trying to help you. And that’s worth more to them long term than the commission they gave up.
That salesperson also acted as a filter. Instead of dragging you through a process that was never going to end in the right car for you, they shut it down early. “I’d rather figure out this isn’t a fit now than waste three weeks pretending it is.” That’s a valuable thing to do for someone, even though it feels like giving something up.
Why Helping Beats Selling, Long Term
This is the part that’s easy to say and hard to actually do, because losing a sale on purpose feels like losing. In the short term, it is. You made zero dollars off that interaction.
But sales isn’t a single transaction. Every time you choose the customer’s actual interest over your immediate interest, you’re making a deposit into something that pays out later.
Think about what actually happens when you recommend someone to a friend. You’re putting your own reputation behind them. That’s why referrals carry so much more weight. A good salesperson isn’t just building a customer list over time, they’re building a reputation, and reputation compounds in a way a single sale never does. One good interaction turns into a repeat customer, who turns into a referral, who turns into a new customer, who eventually refers someone else. You didn’t sell that next person anything. Your reputation did.
The pushy salesperson is optimizing for the next ten minutes. The good salesperson is optimizing for the next ten years. Those two strategies look completely different in the moment and completely different in the results they produce.
This matters more now than it used to. Buyers have more information than ever. They can research a product, compare prices, and read reviews before they ever talk to a person. Information used to be the salesperson’s advantage. It isn’t anymore. What’s left as the differentiator is trust, and trust isn’t something you can fake your way into. You either have a track record of putting the customer’s interest first, or you don’t.
The Real Job of a Salesperson
The stigma exists because plenty of salespeople treat the sale as the goal. But I think the sale is really just a byproduct of solving someone’s problem.
Once you flip that order, being “salesy” stops making much sense.
The job isn’t to convince someone to buy. It’s to figure out what’s actually going on, understand what they need, and help them make a good decision. Good sales is really just good diagnosis.
Sometimes that decision helps you.
Sometimes it sends them to a competitor.
Sometimes the answer is that they shouldn’t buy anything at all.
And that’s okay.
I think that’s what I misunderstood about sales when I was younger. I thought the best salesperson was the person who could convince anyone to buy. Now I think it’s the person who can understand a problem well enough to know whether they should buy in the first place.
Sometimes the best thing you can do in sales is tell someone, “You probably shouldn’t buy this.” That’s probably the least salesy thing you can do. Ironically, it’s probably one of the best ways to become someone people trust when they are ready to buy something.
– Croy